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Synlett 1998; 1998(12): 1414-1416
DOI: 10.1055/s-1998-1960
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Asymmetric α-Alkylation of α,β-Unsaturated Esters. Application to the Synthesis of (R)-Lavandulol, (R)-Sesquilavandulol and Related Trifluoromethyl Compounds

S. Faure* , O. Piva
  • *UMR 6519 C.N.R.S. "Réactions sélectives et applications", UFR Sciences - Université de Reims - Champagne - Ardenne, B.P. 1039 - 51687 Reims cedex - France; Fax 00 33 (0)3 26 05 31 66; E-mail: olivier.piva@univ-reims.fr.
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Publication Date:
31 December 2000 (online)

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Diastereoselective α-alkylation/deconjugation of esters of diacetone D-glucose has been performed and applied to the syntheses of (R)-lavandulol, (R)-sesquilavandulol with de up to 74%. The same reaction performed with trifluoromethyl derivatives was also achieved but without significant diastereoselectivity.

lavandulol - sesquilavandulol - asymmetric alkylation - diacetone D-glucose - trifluoromethyl compounds

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